Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

Eschenmoser-Claisen Rearrangement

Sandmeyer reaction   Named Reactions in Organic Synthesis

Reaction category:
Pericyclic and photochemical reactions

Other featured pericyclic reactions:
Featured photochemical reactions:


In 1964 the Swiss chemist Albert Eschenmoser reported that allylic or benzylic alcohols heated in the presence of N,N-dimethylacetamide dimethyl acetal in xylenes underwent a form of Claisen rearrangement. This generated a γ,δ-unsaturated amide with a high level of stereospecificity, and today this transformation has become known as the Eschenmoser - Claisen rearrangement.

This rearrangement typically occurs at lower temperatures, between 100-150 degrees centigrade, than other variants such as the Claisen rearrangement itself and is more (E) - selective.

During the first total synthesis of (±)-Stenine by D.J.Hart and colleagues, one of the key steps was an Eschenmoser - Claisen rearrangement that afforded a key amide intermediate in 93% yield.


Mechanism of the Eschenmoser-Claisen rearrangement:

mechanism of the Eschenmoser-Claisen rearrangement
Which is your favorite named reaction?   Vote now

Find your reagents and pack sizes


Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions


Transition metal-catalyzed couplings


Reactions involving carbonyl compounds

Reduction reactions

Rearrangement reactions

Electrophilic addition reactions

Some relevant Alfa Aesar products for the Eschenmoser-Claisen rearrangement:

N,N-Dimethylacetamide dimethyl acetal, tech. 90%, stab with 5-10% methanol
Xylenes, mixed, 97+%
Xylenes, ACS, 98.5+% (Assay, isomers plus ethylbenzene

We have many allylic and benzylic alcohols in our portfolio.




Life Science

Metals & Materials


Analytical & Labware